This paper describes how the gaming of society’s rules by corporations contributes to the problem of institutional corruption in the world of business. “Gaming” in its various forms involves the use of technically legal means to subvert the intent of society’s rules in order to gain advantage over rivals, maximize reported earnings, maintain high credit ratings, preserve access to capital on favorable terms, and reap personal rewards - just mention several possible motives. It is one of the most corrosive forms of institutional corruption in business. “Institutional corruption” refers to company-sanctioned behavior and relationships that may be lawful but either harm the public interest or weaken the capacity of the institution to achieve its primary purposes. The most salient consequence of institutional corruption is diminished public trust in the governance of the institution. In this paper, I describe the twin phenomena of gaming and institutional corruption - and how the former contributes to the latter, often with the support of professional advisors at law and auditing firms. I illustrate these phenomena with examples from Enron, which (apart from outright fraud) pursued one of the greatest gaming strategies of all time. I also point to the implementation of the Dodd-Frank Act as an excellent source of clinical data pertaining to gaming in a more contemporary setting. I then discuss how gaming and other trust-destroying behavior have been encouraged by the short-term decision-making horizons of both corporate executives and managers of large investment funds, how those time horizons are largely driven by ways in which the performance of operating executives and investment fund managers is measured and rewarded, and how the directors of these entities become complicit in the gaming of society’s rules and the spreading of institutional corruption. I end by suggesting possible remedies for curbing the ill effects of continued gaming of society’s rules and restoring much needed public trust in the offending institutions.